Former Chicago Bears quarterback Jay Cutler, 41, has found love once again, this time with Samantha Robertson. The couple, who have been dating for several years, made their engagement public after Robertson was spotted wearing a stunning ring during the Yellowstone season 5B premiere on November 7, per TMZ. The news of their engagement has been confirmed by multiple sources close to the couple, who have enjoyed a relatively private romance until now.

The couple’s relationship began shortly after Cutler's split from his ex-wife, reality star Kristin Cavallari, with whom he shares three children: Camden, 12, Jaxon, 10, and Saylor, 8. Cutler and Cavallari married in 2013 but separated in 2020. Despite their breakup, both have maintained a healthy co-parenting relationship for the sake of their children, a dynamic that Cavallari openly expressed support for. In a 2022 podcast appearance, Cavallari shared that she wished Cutler happiness, even hoping he would remarry one day.

Cutler and Robertson’s engagement is the latest chapter in a relationship that has slowly unfolded over the last three years. Their bond has been increasingly public in 2023, with Robertson sharing photos on social media, including a romantic snap of the couple at a friend’s wedding in France. The trip was a key moment in their relationship, with Robertson captioning one post with “Vive la France” and congratulating the newlyweds, marking the couple’s growing connection.

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Samantha Robertson's Past and Future

Before her relationship with Cutler, Robertson was married to actor and fashion designer Trace Ayala. The couple shares two daughters, Sophia and River. Robertson, like Cutler, has moved forward from her previous marriage and embraced her new chapter with Cutler.

The pair’s engagement comes at a time when Cutler’s co-parenting relationship with Cavallari has reached a positive place. In a recent interview, Cavallari discussed the emotional challenges of her marriage to Cutler, expressing how difficult it was to leave but also acknowledging that she tried everything to make it work. She emphasized that her priority now is ensuring the happiness of their children, showing maturity and grace in the face of her past relationship.

As for Jay Cutler and Robertson, their engagement marks the beginning of a new journey together. The couple is sure to face the future with a strong foundation built on love, understanding, and their shared experiences. With their love in the spotlight, fans are eager to see what comes next for this blended family.